Selective fluorescence sensing of cyanide with an o-(carboxamido)trifluoroacetophenone fused with a cyano-1,2-diphenylethylene fluorophore

A fluorescence probe based on an o-(carboxamido)trifluoroacetophenone binding motif shows selective fluorescence quenching toward cyanide among various anions examined. In particular, the probe responds only to cyanide in aqueous media. A novel fluorescence probe has been synthesized, which consists...

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Bibliographic Details
Published in:Tetrahedron letters 2008-09, Vol.49 (38), p.5544-5547
Main Authors: Lee, Hanna, Chung, Yun Mi, Ahn, Kyo Han
Format: Article
Language:English
Subjects:
Anion sensing
Cyanide sensing
Fluorescence probe
o-(Carboxamido)trifluoroacetophenone
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Summary:A fluorescence probe based on an o-(carboxamido)trifluoroacetophenone binding motif shows selective fluorescence quenching toward cyanide among various anions examined. In particular, the probe responds only to cyanide in aqueous media. A novel fluorescence probe has been synthesized, which consists of o-(carboxamido)trifluoroacetophenone moiety as the recognition element and cyano-1,2-diphenylethylene moiety as the signaling unit. Fluorescence titrations of the probe with anions such as F −, Cl −, I −, CN −, SCN −, AcO −, H 2 PO 4 - , HSO 4 - , and ClO 4 - as their Bu 4N + salts in acetonitrile show that CN − is the most efficient quencher, AcO − and F − follow it, and other anions show little changes. In an aqueous medium, MeOH–water (9:1), the probe shows fluorescence quenching only toward cyanide and no changes toward the other anions.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.07.065